3483-18-9

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-Methylphenyl)-1,2,3-oxadiazole-3-ium-5-olate is used as a pharmaceutical intermediate for the synthesis of various bioactive compounds. Its unique structure and electronic properties make it a promising candidate for the development of new drugs with improved potency and selectivity.
Used in Agrochemical Industry:
3-(2-Methylphenyl)-1,2,3-oxadiazole-3-ium-5-olate is used as a key intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and heterocyclic nature allow for the creation of novel molecules with enhanced biological activity and selectivity towards target pests or weeds.
Used in Material Science:
3-(2-Methylphenyl)-1,2,3-oxadiazole-3-ium-5-olate is used as a building block for the development of new materials with unique properties. Its electron-deficient nature and aromaticity can contribute to the formation of conjugated systems, which are essential for applications in optoelectronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs).
Used in Catalyst Design:
3-(2-Methylphenyl)-1,2,3-oxadiazole-3-ium-5-olate is used as a catalyst or catalyst precursor in various chemical reactions. Its reactivity and electronic properties can be tuned to promote specific transformations, enhancing the efficiency and selectivity of chemical processes.

InChI:InChI=1/C9H8N2O2/c1-7-4-2-3-5-8(7)11-6-9(12)13-10-11/h2-6H,1H3

Upstream product

• 90557-96-3 N-nitroso-N-o-tolyl-glycine 
• 508191-77-3 3-phenylsydnone 
• 74-88-4 methyl iodide 
• 21911-61-5 N-(2-methylphenyl)glycine 
• 95-53-4 o-toluidine 

Downstream Products

• 60642-49-1 3,3'-di-o-tolyl-4,4'-sulfanediyl-bis-sydnone 
• 21074-17-9 4-bromo-3-o-tolylsydnone 
• 72913-07-6 4-acetyl-3-(2-methylphenyl)sydnone 
• 85795-86-4 3-o-Tolylsydnone-4-sulfonamide 
• 85795-87-5 C₁₀H₁₁N₃O₄S 
• 85795-89-7 C₁₁H₁₃N₃O₄S 
• 85795-88-6 C₁₁H₁₃N₃O₄S 
• 85795-90-0 3-o-Tolylsydnone-4-(N-diethyl)sulfonamide 
• 85795-94-4 C₁₃H₁₅N₃O₄S 
• 85795-91-1 C₁₃H₁₇N₃O₄S 
• 85795-92-2 C₁₄H₁₇N₃O₄S 
• 85795-93-3 C₁₃H₁₅N₃O₅S 
• 269392-83-8 5-methyl-3-o-tolyl-3H-[1,3,4]oxadiazol-2-one 
• 85795-82-0 3-o-Tolylsydnone-4-sulfonylchloride 

Relevant academic research and scientific papers

One-pot conversion of N-arylglycines to sydnones efficiently promoted by bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex Cl2-dabco in the presence of NaNO2/Ac2O under neutral condition

Bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex, (Cl2-DABCO), has been found as an active chlorine complex for effective one-pot conversion of various N-arylglycines to sydnones in high yields (85-95%) under mild and neutral condition.

Synthesis and evaluation of phenyl substituted sydnones as potential DPPH-radical scavengers

A series of phenyl substituted sydnones has been synthesized and their radical-scavenging activity has been studied on DPPH free radical. Out of eighteen compounds screened, nine compounds show interesting activity. A mechanism is presented whereby sydnones scavenge DPPH radical through donating H-atom at 4th-position. Its strong radical-scavenging activity mainly arises from 1, 2, 3-oxadiazolium-5-olate ring. Different substituents and their positions on the phenyl ring differently influence DPPH scavenging activity and therefore, may provide clues to design and develop better free-radical scavenging sydnones with multiple activities.

Microwave-assisted synthesis of N-arylglycines: Improvement of sydnone synthesis

Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS) as an efficient promoter for one-pot conversion of N-arylglycines to sydnones in the presence of NaNO2/Ac2O under neutral conditions

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS)-promoted one-pot conversion of various N-arylglycines to sydnones using a combination of NaNO2 and Ac2O has been achieved efficiently through N-nitrosation followed by cyclization

Catalytic activity of 1,3-dibromo-5,5-dimethylhydantoin (DBH) in the one-pot transformation of N-arylglycines to N-arylsydnones in the presence of NaNO2/Ac2O under neutral conditions: Subsequent bromination of these sydnones to their

1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO2 and Ac 2O in high yields (80-

The sydnone ring as an ortho-director of lithiation. 2. Dilithiation of 3-phenylsydnone and regiospecific @?o-aryl acylation using N-methoxy-N-methylamides

Readily available 3-phenylsydnone (1) reacts with n-butyllithium/TMEDA to form the dilithio species 2 which can be regiospecifically acylated at the ortho-aryl position using N-methoxy-N-methylamides (Weinreb's amides).

The Efficient Synthesis of 3-Arylsydnones Under Neutral Conditions

Various substituted aryl sydnones can be prepared in high yield under mild, neutral conditions by nitrosation of the appropriate aryl glycine with isoamyl nitrite in dimethoxyethane followed by cyclization with trifluoroacetic anhydride.